607-55-6Relevant academic research and scientific papers
Synthesis, characterization, antioxidant evaluation, molecular docking and density functional theory studies of phenyl and naphthyl based esters
Akhter, Zareen,Asghar, Muhammad Adeel,Ismail, Hammad,Kalsoom, Saima,Liaqat, Faroha,Mckee, Vickie,Sabir, Shaista,Sani, Asma,Shabbir, Muhammad,Zaib-un-Nisa
, (2020)
Two phenol based esters phenyl benzoate (OE1) and 1-naphthyl benzoate (OE2) were synthesized from phenol/1-naphthol and benzoyl chloride respectively. The structural elucidation of the synthesized compounds was accomplished by spectroscopic studies (FTIR, 1H NMR & GC-MS) and single crystal X-ray diffraction analysis. DPPH (2, 2-diphenyl-1-picryl-hydrazyl-hydrate) free radical and hydrogen peroxide activities were performed to evaluate the antioxidant capabilities of the synthesized esters. The compounds (OE1 & OE2) showed DPPH scavenging activity in concentration dependent manner with IC50 values 605.6 μM and 1138.7 μM correspondingly. Similarly, in hydrogen peroxide assay, OE1 and OE2 exhibited moderate activity with IC50 values 1510.2 μM and 1069.4 μM respectively. Molecular docking of the compounds was carried out to predict their antioxidant binding mechanism against target protein using the MOE suite. The structure?activity relationship analysis showed that replacing the phenyl ring by naphthyl significantly influences their activity. Geometrical studies of the compounds have been performed by both semi-empirical and DFT methods; results reveal an excellent convergence of experimental and theoretical structural parameters. A detailed bonding investigation of each compound has been performed by NBO and Bader's AIM analysis to obtain inter and intramolecular interactions.
Metal-Free Selective Modification of Secondary Amides: Application in Late-Stage Diversification of Peptides
Adebomi, Victor,Sriram, Mahesh,Streety, Xavier,Raj, Monika
supporting information, p. 6189 - 6193 (2021/08/01)
Here we solve a long-standing challenge of the site-selective modification of secondary amides and present a simple two-step, metal-free approach to selectively modify a particular secondary amide in molecules containing multiple primary and secondary amides. Density functional theory (DFT) provides insight into the activation of C-N bonds. This study encompasses distinct chemical advances for late-stage modification of peptides thus harnessing the amides for the incorporation of various functional groups into natural and synthetic molecules.
Hydrogen-bond-assisted transition-metal-free catalytic transformation of amides to esters
Huang, Changyu,Li, Jinpeng,Wang, Jiaquan,Zheng, Qingshu,Li, Zhenhua,Tu, Tao
, p. 66 - 71 (2020/11/18)
The amide C-N cleavage has drawn a broad interest in synthetic chemistry, biological process and pharmaceutical industry. Transition-metal, luxury ligand or excess base were always vital to the transformation. Here, we developed a transition-metal-free hydrogen-bond-assisted esterification of amides with only catalytic amount of base. The proposed crucial role of hydrogen bonding for assisting esterification was supported by control experiments, density functional theory (DFT) calculations and kinetic studies. Besides broad substrate scopes and excellent functional groups tolerance, this base-catalyzed protocol complements the conventional transition-metal-catalyzed esterification of amides and provides a new pathway to catalytic cleavage of amide C-N bonds for organic synthesis and pharmaceutical industry. [Figure not available: see fulltext.]
Nucleophilic aromatic substitution of unactivated fluoroarenes enabled by organic photoredox catalysis
Nicewicz, David A.,Pistritto, Vincent A.,Schutzbach-Horton, Megan E.
supporting information, p. 17187 - 17194 (2020/11/02)
Nucleophilic aromatic substitution (SNAr) is a classical reaction with well-known reactivity toward electron-poor fluoroarenes. However, electron-neutral and electron-rich fluoro(hetero)arenes are considerably underrepresented. Herein, we present a method for the nucleophilic defluorination of unactivated fluoroarenes enabled by cation radical-accelerated nucleophilic aromatic substitution. The use of organic photoredox catalysis renders this method operationally simple under mild conditions and is amenable to various nucleophile classes, including azoles, amines, and carboxylic acids. Select fluorinated heterocycles can be functionalized using this method. In addition, the late-stage functionalization of pharmaceuticals is also presented. Computational studies demonstrate that the site selectivity of the reaction is dictated by arene electronics.
Nickel-Catalyzed Cross-Coupling of Aryl Redoxactive Esters with Aryl Zinc Reagents
Shih, Bo-Hao,Basha, R. Sidick,Lee, Chin Fa
, p. 8862 - 8866 (2019/09/30)
A nickel-catalyzed aryl-aroyloxyl C(sp2)-O radical cross-coupling reaction conducted using a redox active ester with aryl zinc reagent was developed. This method demonstrates a new disconnection approach for formation of aryl aryl esters. In the one-pot sequential process, the readily available aryl carboxylic acids can be converted into functionalized aryl aryl esters and heteroaryl esters. This protocol is amenable to the gram-scale synthesis. The present method has a wide substrate scope and high functional group tolerance.
Preparation method for synthesis of phenolic ester through thiocarboxylic acid mediated visible light catalyzed phenol acylation reaction
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Paragraph 0017; 0018; 0056; 0057; 0058, (2018/07/30)
The invention discloses a preparation method for synthesis of phenolic ester through a thiocarboxylic acid mediated visible light catalyzed phenol acylation reaction. Thiocarboxylic acid compounds andphenol compounds are subjected to a site specific reaction under certain conditions to produce phenolic ester compounds, wherein the certain conditions are as follows: under the conditions of normaltemperature, normal pressure and visible light, K2CO3 is used as an alkaline catalyst, terpyridyl ruthenium dichloride hexahydrate is used as a photosensitizer and acetonitrile is used as a reaction solvent. Synthesis of phenolic ester under catalysis of visible light is realized, thiocarboxylic acid is used as an acylation reagent, and the site specific phenol esterification reaction is realizedefficiently under mild conditions of normal temperature, normal pressure and visible light. The method has mild reaction conditions, large substrate functional group tolerance, high applicability andhigh yield, and an efficient, reliable and economical preparation method is provided for synthesis of phenolic ester.
Acceptorless Dehydrogenation of Hydrocarbons by Noble-Metal-Free Hybrid Catalyst System
Fuse, Hiromu,Kojima, Masahiro,Mitsunuma, Harunobu,Kanai, Motomu
supporting information, p. 2042 - 2045 (2018/04/16)
A hybrid catalysis that comprises an acridinium photoredox catalyst, a thiophosphate organocatalyst, and a nickel catalyst-enabled acceptorless dehydrogenation of hydrocarbons is reported. The cationic nickel complex played a critical role in the reactivity. This is the first example of acceptorless dehydrogenation of hydrocarbons by base metal catalysis under mild reaction conditions of visible light irradiation at room temperature.
Sodium cyanide-promoted copper-catalysed aerobic oxidative synthesis of esters from aldehydes
Nowrouzi, Najmeh,Abbasi, Mohammad,Bagheri, Maryam
, (2017/09/30)
A simple and efficient copper-catalysed procedure for oxidative esterification of aldehydes with alcohols and phenols mediated by sodium cyanide, using air as a clean oxidant, is described. A variety of aromatic aldehydes and structurally different alcohols and phenols reacted efficiently, and the product esters were obtained in good to excellent yields under normal atmospheric and solvent-free conditions.
Palladium-Catalyzed Oxidative Carbonylation of Aryl Hydrazines with CO and O2 at Atmospheric Pressure
Tu, Yongliang,Yuan, Lin,Wang, Tao,Wang, Changliu,Ke, Jiamei,Zhao, Junfeng
, p. 4970 - 4976 (2017/05/12)
Palladium-catalyzed aerobic oxidative aminocarbonylation and alkoxycarbonylation reactions with aryl hydrazines as coupling partners have been developed. The oxidative carbonylation of aryl hydrazines proceeded smoothly at atmospheric pressure CO, employi
Asymmetric Oxidative Cycloetherification of Naphtholic Alcohols
Jain, Nikita,Xu, Sanjia,Ciufolini, Marco A.
supporting information, p. 4542 - 4546 (2017/04/13)
The catalytic, enantioselective oxidative cyclization of naphthol-derived carboxylic acids mediated by chiral hypervalent iodine reagents has been studied extensively in the recent past, but analogous reactions of non-carboxylic substrates are yet unknown. This paper describes a catalytic, enantioselective, hypervalent iodine-promoted oxidative cycloetherification reaction of naphtholic alcohols. The new process relies on a variant of the Uyanik–Ishihara catalyst, in which the stereogenic centers have been relocated closer to the iodine atom. The new catalyst design affords optical yields comparable to those available with Uyanik–Ishihara iodides, but chemical yields are sensibly higher, at least with the tests substrates. An even more problematic reaction is the catalytic, enantioselective oxidative cyclization of naphtholic sulfonamides. In this case, the new catalyst affords significantly higher optical inductions than Uyanik–Ishihara iodides. The kinetic resolution of particular naphtholic alcohols is demonstrated. The absolute configuration of a numver of enantioenriched compounds obtained in this study was ascertained by X-ray diffractometry.
